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A Formal Synthesis of Porantheridine and an Epimer

descriptionPublicationkeyboard_double_arrow_right Article 25 Nov 2009 English Publisher:American Chemical Society (ACS)Journal:The Journal of Organic Chemistry, volume 74, pages 9,460-9,465 (issn: 0022-3263, eissn: 1520-6904, Copyright policy )
Authors: Roderick W, Bates; Yongna, Lu;

doi: 10.1021/jo9021925

pmid: 19938834

A Formal Synthesis of Porantheridine and an Epimer

Abstract

A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-isoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method.

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Keywords

Silver, Acylation, Stereoisomerism, Catalysis, Alkadienes, Alkaloids, Models, Chemical, Cyclization, Solvents, Gold, Imines, Oxazoles

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Powered by OpenAIRE graph
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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
48
Top 10%
Top 10%
Top 10%
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